1-Methylcyclohexanecarboxylic acid → HCID 58483286, compound

HRID 1846072Notes

Reaction equation

HRID 1846072 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:23][C:24]1([C:30](O)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[NH2:33][CH2:34][C:35]1[CH:36]=[CH:37][C:38]([CH3:44])=[C:39]([CH:43]=1)[C:40]([OH:42])=[O:41]>CN(C=O)C>[CH3:44][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][NH:33][C:30]([C:24]2([CH3:23])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:31])=[CH:43][C:39]=1[C:40]([OH:42])=[O:41]

Participants

5

Reactant 3

HCID 707441-Methylcyclohexanecarboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 20378367HCID 20378367, compound

Product 1

HCID 58483286HCID 58483286, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TBTU (15 mmol; 4.9 g) was added to a mixture of 1-methylcyclohexylcarboxylic acid (15 mmol; 2.2 g), TEA (9.6 mL) and DMF (130 mL) at rt. After 10 min a mixture of 5-aminomethyl-2-methylbenzoic acid (6.3 g crude mixture with NaCl, see step (b) above) was added. After 3 h at rt the reaction mixture was concentrated, water was added and the formed precipitate was washed with water, dried and purified by preparative HPLC. Yield: 3.6 g (83%). MS [M+H]+=290; TLC: Rf=0.49 (silica gel, DCM:EtOH 9:1).

Workup

  1. additionwas added
  2. concentrationAfter 3 h at rt the reaction mixture was concentrated
  3. additionwater was added
  4. washthe formed precipitate was washed with water
  5. customdried
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-8fc5afedfc4e48e9998751723447930f
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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